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WO2010067745A1 - Feuille adhésive - Google Patents

Feuille adhésive Download PDF

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Publication number
WO2010067745A1
WO2010067745A1 PCT/JP2009/070315 JP2009070315W WO2010067745A1 WO 2010067745 A1 WO2010067745 A1 WO 2010067745A1 JP 2009070315 W JP2009070315 W JP 2009070315W WO 2010067745 A1 WO2010067745 A1 WO 2010067745A1
Authority
WO
WIPO (PCT)
Prior art keywords
pressure
sensitive adhesive
adhesive sheet
reactive group
meth
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2009/070315
Other languages
English (en)
Japanese (ja)
Inventor
隆行 荒井
仁 又野
クリスティアン ルスリム
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lintec Corp
ASM Inc
Original Assignee
Lintec Corp
Advanced Softmaterials Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lintec Corp, Advanced Softmaterials Inc filed Critical Lintec Corp
Priority to CN2009801494788A priority Critical patent/CN102245726A/zh
Priority to US13/133,731 priority patent/US20110262746A1/en
Priority to EP09831849A priority patent/EP2377904A1/fr
Publication of WO2010067745A1 publication Critical patent/WO2010067745A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
    • C03C27/06—Joining glass to glass by processes other than fusing
    • C03C27/10—Joining glass to glass by processes other than fusing with the aid of adhesive specially adapted for that purpose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
    • C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
    • C08G18/8029—Masked aromatic polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/007—Polyrotaxanes; Polycatenanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/16—Cyclodextrin; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2170/00—Compositions for adhesives
    • C08G2170/40—Compositions for pressure-sensitive adhesives
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2201/00—Constructional arrangements not provided for in groups G02F1/00 - G02F7/00
    • G02F2201/54—Arrangements for reducing warping-twist
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2839—Web or sheet containing structurally defined element or component and having an adhesive outermost layer with release or antistick coating
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852—Adhesive compositions
    • Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852—Adhesive compositions
    • Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
    • Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof

Definitions

  • the present invention relates to a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer suitable for optical applications and excellent in stress relaxation and durability.
  • a pressure-sensitive adhesive layer formed from a pressure-sensitive adhesive composition is often used to adhere a polarizing plate or a retardation plate to a glass substrate or the like.
  • optical members such as polarizing plates and retardation plates are easily shrunk by heat, etc.
  • shrinkage occurs due to thermal history, and as a result, the adhesive layer laminated on the optical member cannot follow the shrinkage.
  • Problems have been pointed out, such as peeling at the interface (so-called floating or peeling), or light leakage (so-called white spots) due to displacement of the optical axis of the optical member due to stress during contraction of the optical member. .
  • (1) a method of suppressing the contraction of the optical member itself by bonding a pressure-sensitive adhesive layer having high adhesive strength and excellent shape stability to an optical member such as a polarizing plate.
  • (2) a method using a pressure-sensitive adhesive layer having a small stress when the optical member is contracted.
  • the method (1) it is effective to use a pressure-sensitive adhesive layer having a high storage elastic modulus as disclosed in Patent Document 1.
  • the method (2) it is effective to use a pressure-sensitive adhesive layer having excellent stress relaxation properties that can flexibly cope with deformation.
  • conventionally when it was attempted to form such an adhesive layer having excellent stress relaxation properties, it was necessary to extremely reduce the crosslinking density in the adhesive layer. If it does so, there existed a problem that the intensity
  • Patent Documents 2 to 4 the pressure-sensitive adhesive composition obtained by adding a plasticizer, liquid paraffin, urethane elastomer or the like to the acrylic pressure-sensitive adhesive instead of extremely reducing the crosslinking density of the pressure-sensitive adhesive layer
  • the pressure-sensitive adhesive layer is given a stress relaxation property, thereby preventing light leakage and durability.
  • the pressure-sensitive adhesive layer formed of a pressure-sensitive adhesive composition to which a plasticizer or liquid paraffin is added has various problems such as the plasticizer and liquid paraffin bleed out over time and the liquid crystal cell is contaminated. It was happening.
  • the pressure-sensitive adhesive composition to which a urethane elastomer is added since the amount of the urethane elastomer is limited from the viewpoint of compatibility with other components, the improvement of the stress relaxation property is insufficient, and the acrylic composition Depending on the compatibility between the adhesive and the urethane elastomer, problems such as white turbidity have occurred.
  • Patent Document 5 proposes a pressure-sensitive adhesive composition in which a polyrotaxane and, if desired, an isocyanate compound are blended in a pressure-sensitive adhesive.
  • JP 2006-235568 A Japanese Patent Laid-Open No. 5-45517 JP-A-9-137143 JP 2005-194366 A JP 2007-224133 A
  • the pressure-sensitive adhesive layer formed from the above-mentioned pressure-sensitive adhesive composition has excellent stress relaxation properties due to polyrotaxane, the optical properties such as total light transmittance and durability were insufficient for optical members.
  • An object of the present invention is to provide a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer that has excellent properties and, in turn, excellent light leakage prevention properties, and also has excellent durability.
  • the present invention has a structure in which a linear molecule penetrates a base material and at least two cyclic molecule openings, and the cyclic molecule has one or more reactive groups.
  • the holding strength according to JIS Z0237 is 70,000 seconds except that the elongation at break of the layer is 300% or more and the haze value is 30% or less, and the measurement temperature of the pressure-sensitive adhesive sheet is 80 ° C.
  • a pressure-sensitive adhesive sheet characterized in that the amount of displacement of the subsequent pressure-sensitive adhesive sheet is 1000 ⁇ m or less (Invention 1).
  • the pressure-sensitive adhesive sheet according to the invention contains the polyrotaxane (A) and satisfies the above physical properties
  • the adhesive sheet is applied to an optical member such as a polarizing plate or a retardation plate. While satisfactorily satisfying optical characteristics such as light transmittance, it is excellent in stress relaxation, and thus in light leakage prevention properties, and also in durability.
  • the said adhesive composition contains the (meth) acrylic acid ester copolymer (B) obtained by copolymerizing a (meth) acrylic acid ester and a reactive group containing monomer. It is preferable to do this (Invention 2).
  • the (meth) acrylic acid ester copolymer (B) is (meth) such that the ratio of the reactive group-containing monomer in the copolymer is 0.01 to 15% by mass.
  • a copolymer obtained by copolymerizing an acrylate ester and a reactive group-containing monomer is preferred (Invention 3).
  • the said adhesive composition can react with the reactive group which the said polyrotaxane (A) has, and the reactive group which the said (meth) acrylic acid ester copolymer (B) has It is preferable to further contain a crosslinking agent (C) having a reactive group (Invention 4).
  • the equivalent ratio of the reactive group of the crosslinking agent (C) to the reactive group of the polyrotaxane (A) is 0.1 to 5, and the copolymer of the (meth) acrylic acid ester It is preferable that the equivalent ratio of the reactive group of the crosslinking agent (C) to the reactive group of the coalescence (B) is 0.001 to 2 (Invention 5).
  • the gel fraction of the pressure-sensitive adhesive layer is preferably 20 to 90% (Invention 6).
  • the reactive group of the polyrotaxane (A) is a hydroxy group
  • the reactive group of the (meth) acrylic acid ester copolymer (B) is a hydroxy group
  • the crosslinking agent (C ) Is preferably an isocyanate group (Invention 7).
  • the substrate may be composed of a release sheet (Invention 8), the substrate may be composed of an optical member (Invention 9), or the substrate is polarized light. It may consist of a plate or a phase difference plate (Invention 10).
  • a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer excellent in durability can be obtained.
  • the pressure-sensitive adhesive sheet according to one embodiment of the present invention has a base material and a pressure-sensitive adhesive layer formed on the base material using the pressure-sensitive adhesive composition, and is in contact with the base material of the pressure-sensitive adhesive layer.
  • the surface on the side that is not present may or may not have a release sheet.
  • Other layers may be interposed between the base material and the pressure-sensitive adhesive layer.
  • the elongation at break of the pressure-sensitive adhesive layer is 300% or more
  • the haze value of the pressure-sensitive adhesive layer is 30% or less
  • It is a requirement that the holding force of the pressure-sensitive adhesive sheet is 1000 ⁇ m or less as a deviation amount after 70,000 seconds at 80 ° C.
  • the above requirement (1) indicates a so-called extending pressure-sensitive adhesive layer rich in stress relaxation.
  • the above requirement (3) is satisfied with a so-called hard pressure-sensitive adhesive layer having a low stress relaxation property, but the conventional pressure-sensitive adhesive layer rich in stress relaxation property falls due to cohesive failure or the like.
  • the holding force (deviation amount) cannot be measured. That is, in the conventional pressure-sensitive adhesive layer, there is no pressure-sensitive adhesive layer that satisfies both the above requirements (1) and (3) at the same time.
  • satisfying both of the above requirements (1) and (3) means that the polyrotaxane (A) having mobility is extended to a certain amount by using the polyrotaxane (A) as a crosslinking point. Indicates that it has a cohesive force like a so-called hard adhesive layer.
  • the above requirement (2) defines the compatibilization performance of the polyrotaxane (A) and other components (particularly the (meth) acrylic acid ester copolymer (B) described later), and satisfies this requirement. Thus, it is possible to prevent an adverse effect on the adhesive performance due to too much polyrotaxane (A).
  • the pressure-sensitive adhesive sheet When the pressure-sensitive adhesive sheet satisfies all the above requirements, when the pressure-sensitive adhesive sheet is applied to an optical member such as a polarizing plate or a phase difference plate, the pressure-sensitive adhesive sheet sufficiently satisfies optical characteristics such as total light transmittance. In addition, it has excellent stress relaxation properties, and thus excellent light leakage prevention properties, and also has excellent durability.
  • the breaking elongation of the pressure-sensitive adhesive layer is 300% or more, preferably 500% or more. When the elongation at break of the pressure-sensitive adhesive layer is 300% or more, the pressure-sensitive adhesive layer is excellent in both stress relaxation properties and durability.
  • the measuring method of the breaking elongation of the pressure-sensitive adhesive layer is as described in the test examples described later.
  • the haze value of the pressure-sensitive adhesive layer indicates the degree to which the polyrotaxane (A) is compatible with other components (particularly the (meth) acrylic acid ester copolymer (B) described later). When the ratio of polyrotaxane (A) is too large, it tends to show a high value.
  • the haze value of the pressure-sensitive adhesive layer in this embodiment is usually 30% or less, preferably 25% or less, and particularly preferably 0 to 6%.
  • the haze value of the pressure-sensitive adhesive layer exceeds 30%, the compatibility of the polyrotaxane (A) with other components may be hindered, thereby adversely affecting the pressure-sensitive adhesive performance and reducing the durability of the pressure-sensitive adhesive sheet.
  • the haze value of the pressure-sensitive adhesive layer is 30% or less, the pressure-sensitive adhesive sheet has durability and the transparency of the pressure-sensitive adhesive layer is high, which is suitable for application to an optical member. For example, a display with high definition and high visibility can be obtained by the present adhesive sheet. If the haze value exceeds 30%, the pressure-sensitive adhesive layer may become cloudy. In this case, the visibility of the display is lowered.
  • the total light transmittance of the pressure-sensitive adhesive layer is preferably 70% or more, particularly preferably 85% or more from the viewpoint of obtaining good visibility.
  • the pressure-sensitive adhesive layer has such physical properties, it is suitable as an optical member for liquid crystal panels, liquid crystal displays, flexible displays, organic EL displays, electronic papers, and the like.
  • the present adhesive layer has sufficient stress relaxation properties, it has the greatest feature that it does not drop even under a severe condition of a measurement temperature of 80 ° C.
  • the holding force of the pressure-sensitive adhesive sheet is 1000 ⁇ m or less, preferably 800 ⁇ m or less, and particularly preferably 650 ⁇ m or less as a deviation amount.
  • the lower limit value of the shift amount may not be shifted, but in the present pressure-sensitive adhesive layer, it is usually 100 ⁇ m or more and preferably 200 ⁇ m or more because stress relaxation is exhibited.
  • the holding force is a holding force based on JIS Z0237 except that the measurement temperature is 80 ° C., and the shift amount is the shift amount of the pressure-sensitive adhesive sheet after 70,000 seconds. Note that the measurement temperature of 80 ° C. is most clearly different from the conventional pressure-sensitive adhesive layer excellent in stress relaxation (it falls in the conventional pressure-sensitive adhesive layer excellent in stress relaxation). Because.
  • the pressure-sensitive adhesive sheet When the holding force of the pressure-sensitive adhesive sheet is 1000 ⁇ m or less as a displacement amount, the pressure-sensitive adhesive sheet is excellent in durability. Further, when the holding force of the pressure-sensitive adhesive sheet is 100 ⁇ m or more as a deviation amount, the pressure-sensitive adhesive sheet is excellent in stress relaxation properties and, in turn, excellent in light leakage prevention properties.
  • the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer is: A. A polyrotaxane having a linear molecule penetrating through openings of at least two cyclic molecules, the cyclic molecule having one or more reactive groups, and a blocking group at both ends of the linear molecule ( A) Is an essential ingredient, B.
  • Crosslinking agent (C) having a reactive group capable of reacting with a reactive group possessed by (meth) acrylic acid ester copolymer (B) and a reactive group possessed by polyrotaxane (A) It is particularly preferable to further contain
  • the pressure-sensitive adhesive composition containing the three components (A) to (C) will be mainly described, but the present invention is not limited to this.
  • the reactive group possessed by the polyrotaxane (A) is R 1
  • the reactive group possessed by the (meth) acrylic acid ester copolymer (B) is R 2
  • the reactive group possessed by the crosslinking agent (C) is represented by R 3.
  • the pressure-sensitive adhesive composition has linear molecules L penetrating through openings of at least two cyclic molecules T having a reactive group R 1, and both ends of the linear molecules L. It becomes having blocking groups BL polyrotaxane (a), having a reactive group R 2 (meth) acrylic acid ester copolymer (B), and can react with the reactive group R 1 and the reactive group R 2 It can be obtained by blending with a crosslinking agent (C) having a functional group R 3 .
  • the cyclic molecule T freely moves on the linear molecule L of the polyrotaxane (A), so that the pressure-sensitive adhesive layer is rich in stress relaxation properties.
  • the proportion of the reactive group-containing monomer having a reactive group R 2 in the (meth) acrylic acid ester copolymer (B) is preferably 0.01 to 15% by mass.
  • the content is more preferably 0.1 to 10% by mass, and particularly preferably 0.5 to 5% by mass.
  • the proportion of the reactive group-containing monomer is less than 0.01% by mass, a large amount of (meth) acrylic acid ester copolymer (B) in which no reactive group-containing monomer is introduced at the micro level is generated.
  • the physical property values may not be obtained.
  • the (meth) acrylic acid ester copolymers (B) are often directly bonded to each other without using the polyrotaxane (A), or a crosslinked part. Due to the denseness, the stress relaxation property due to the mobility via the polyrotaxane (A) may not be sufficiently obtained.
  • the equivalent ratio of the reactive group R 3 of the crosslinking agent (C) to the reactive group R 1 of the polyrotaxane (A) is preferably 0.1 to 5, and particularly preferably 0.5 to 2.
  • the amount ratio is less than 0.1, since there are many polyrotaxanes (A) that are not crosslinked even when crosslinked by heating or the like, the uncrosslinked polyrotaxane (A) is liberated in a heat-resistant environment, and the pressure-sensitive adhesive layer May become cloudy or foam easily, and durability may be reduced.
  • the amount ratio exceeds 5
  • a different (meth) acrylate copolymer (B) is bonded to each of the many reactive groups R 1 of one cyclic molecule T of the polyrotaxane (A).
  • the polyrotaxane (A) does not become a crosslinking point as a whole, but the cyclic molecule T itself becomes a crosslinking point, and the mobility of the crosslinking point is lost.
  • the formed pressure-sensitive adhesive layer has stress relaxation properties. The light leakage prevention property and durability may be lowered.
  • the equivalent ratio of the reactive group R 3 of the crosslinking agent (C) to the reactive group R 2 of the (meth) acrylic acid ester copolymer (B) is preferably 0.001 to 2, It is more preferably from 005 to 1, and particularly preferably from 0.1 to 0.5.
  • the amount ratio is less than 0.001 since there are many (meth) acrylic acid ester copolymers (B) that are not crosslinked even when subjected to crosslinking by heating or the like, the formed pressure-sensitive adhesive layer is in a heat resistant environment. Foaming is likely to occur, and durability may be reduced.
  • the (meth) acrylic acid ester copolymer (B) has a large number of reactive groups R 2 in one molecule, each of which is cross-linked from multiple directions.
  • the mobility of the ester copolymer (B) is limited, and as a result, the formed pressure-sensitive adhesive layer has a low stress relaxation property, and the light leakage prevention property and durability may be lowered.
  • the equivalent ratio of the reactive groups R 3 of the polyrotaxane to the total amount of the reactive groups R 2 reactive groups R 1 and (meth) acrylic acid ester copolymer (B) of (A), crosslinking agent (C) Is usually from 0.001 to 2, preferably from 0.05 to 1, particularly preferably from 0.1 to 0.5.
  • a pressure-sensitive adhesive layer with a pressure-sensitive adhesive composition containing polyrotaxane (A).
  • A polyrotaxane
  • the blending amount of the polyrotaxane (A) with respect to the (meth) acrylic acid ester copolymer (B) is maintained at the above-mentioned elongation at break and retention. It is preferable to reduce as long as the force is satisfied. If too much polyrotaxane (A) is added to (meth) acrylic acid ester copolymer (B), incompatibility may occur. In that case, the adhesive performance will be adversely affected, resulting in a decrease in durability. Cause it.
  • the blending amount of the polyrotaxane (A) with respect to the (meth) acrylic acid ester copolymer (B) is preferably 0.000001 to 10 and preferably 0.00001 to 5 in mass ratio. More preferred is 0.0001-2.
  • the gel fraction after crosslinking of the pressure-sensitive adhesive composition is preferably 20 to 90%, particularly 40 to 79%. And more preferably 60 to 75%.
  • the gel fraction is less than 20%, the (meth) acrylic acid ester copolymer (B) and the polyrotaxane (A) are not sufficiently cross-linked, and foaming easily occurs in a heat-resistant environment. , Durability may be reduced.
  • the gel fraction exceeds 90%, the mobility of the crosslinking point based on the polyrotaxane (A) is restricted, so that the stress relaxation property may be lowered and the light leakage prevention property may be deteriorated.
  • the pressure-sensitive adhesive composition prevents deterioration of optical properties due to excessive addition of the polyrotaxane (A), and further the linear molecule L through which the cyclic molecule T of the polyrotaxane (A) penetrates.
  • the degree of freedom to move the top is ensured, and an appropriate crosslinking density can be maintained by crosslinking the polyrotaxane (A) and the (meth) acrylic acid ester copolymer (B).
  • the obtained pressure-sensitive adhesive layer is excellent in optical properties such as total light transmittance, and expresses sufficient strength and excellent stress relaxation properties, thereby having excellent durability and light leakage prevention properties. Become.
  • polyrotaxane (A) can be obtained by a conventionally known method (for example, the method described in JP-A-2005-154675).
  • the linear molecule L of the polyrotaxane (A) is a molecule or substance that is included in the cyclic molecule T and can be integrated by a mechanical bond instead of a chemical bond such as a covalent bond. If it is a thing, it will not specifically limit.
  • “linear” of “linear molecule” means substantially “linear”. That is, as long as the cyclic molecule T can move on the linear molecule L, the linear molecule L may have a branched chain.
  • linear molecule L of the polyrotaxane (A) for example, polyethylene glycol, polypropylene glycol, polyisoprene, polyisobutylene, polybutadiene, polytetrahydrofuran, polyacrylic acid ester, polydimethylsiloxane, polyethylene, polypropylene and the like are preferable. Two or more types of linear molecules L may be mixed in the pressure-sensitive adhesive composition.
  • the number average molecular weight of the linear molecule L of the polyrotaxane (A) is preferably 3,000 to 300,000, particularly preferably 10,000 to 200,000, and more preferably 20,000 to 100. 1,000 is preferred. If the number average molecular weight is less than 3,000, the amount of movement of the cyclic molecule T on the linear molecule L becomes small, and the stress relaxation property of the pressure-sensitive adhesive layer may not be sufficiently obtained. Moreover, when a number average molecular weight exceeds 300,000, there exists a possibility that the solubility to the solvent of a polyrotaxane (A) and compatibility with a (meth) acrylic acid ester copolymer (B) may worsen.
  • the cyclic molecule T of the polyrotaxane (A) is not particularly limited as long as it can be included in the linear molecule L and can move on the linear molecule L.
  • “cyclic” of “cyclic molecule” means substantially “cyclic”. That is, as long as it can move on the linear molecule L, the cyclic molecule T may not be completely closed, and may be, for example, a helical structure.
  • Examples of the cyclic molecule T of the polyrotaxane (A) include cyclic polymers such as cyclic polyether, cyclic polyester, cyclic polyetheramine, and cyclic polyamine, or cyclodextrins such as ⁇ -cyclodextrin, ⁇ -cyclodextrin, and ⁇ -cyclodextrin.
  • cyclic polymers such as cyclic polyether, cyclic polyester, cyclic polyetheramine, and cyclic polyamine, or cyclodextrins such as ⁇ -cyclodextrin, ⁇ -cyclodextrin, and ⁇ -cyclodextrin.
  • Specific examples of the cyclic polymer include crown ether or a derivative thereof, calixarene or a derivative thereof, cyclophane or a derivative thereof, cryptand or a derivative thereof.
  • cyclic molecule T As the cyclic molecule T, among the above, since it is relatively easy to obtain and many types of block groups BL can be selected, cyclodextrins such as ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, etc. And ⁇ -cyclodextrin is more preferable. Two or more kinds of these cyclic molecules T may be mixed in the polyrotaxane (A) or the pressure-sensitive adhesive composition.
  • the cyclodextrin may be introduced with a substituent capable of improving the solubility of the polyrotaxane (B).
  • substituents include, for example, an acetyl group, an alkyl group, a trityl group, a tosyl group, a trimethylsilane group, a phenyl group, a polyester chain, an oxyethylene chain, an alkyl chain, an acrylate chain, and the like.
  • the number average molecular weight of the substituent is preferably from 100 to 10,000, particularly preferably from 400 to 2,000.
  • the introduction rate (substitution degree) of the above substituents to the hydroxy group of cyclodextrin is preferably 10 to 90%, particularly preferably 30 to 70%.
  • the introduction rate is less than 10%, the solubility of the polyrotaxane (B) is not sufficiently improved, and when the introduction rate exceeds 90%, the content of the reactive group R 2 in the polyrotaxane (B) becomes low, and the polyrotaxane (B)
  • B) cannot sufficiently react with the copolymer (A) or the crosslinking agent (C).
  • the introduction rate exceeds 90%, the introduction amount may be difficult to control due to steric hindrance.
  • the reactive group R 2 possessed by the cyclic molecule T of the polyrotaxane (B) is preferably, for example, a hydroxy group, a carboxy group, an amino group, etc., and the pressure-sensitive adhesive composition is not biased toward the acidic side or the alkaline side, and is colored by the reaction.
  • a hydroxy group is preferable because it is less likely to occur and the bond stability is excellent.
  • Two or more kinds of these reactive groups R 2 may be mixed in the polyrotaxane (B).
  • the reactive group R 2 may not be directly bonded to the cyclic molecule T. That is, the reactive group R 2 may be present through the substituent.
  • two or more different substituents may be bonded via the reactive group R 2, and any of them may have the reactive group R 2 .
  • the distance from the cyclic molecule T is adjusted to avoid steric hindrance with the cyclic molecule T, and a bulky substituent having a reactive group R 2 is introduced, or the cyclic molecule T Polymerization is performed with the reactive group as a starting point while avoiding the steric hindrance with the alkyl chain, the ether chain, the ester chain, or an oligomer chain thereof, and the reactive group R 2 is added to the substituent. It is also possible to introduce one or more substituents.
  • the hydroxy group present in the cyclodextrin itself is the reactive group R 2 , and when a hydroxypropyl group is added to the hydroxy group, the hydroxy group of the hydroxypropyl group also reacts. Included in the sex group R 2 . Further, when ⁇ -caprolactone is subjected to ring-opening polymerization through the hydroxy group of the hydroxypropyl group, a hydroxy group is formed at the opposite end of the polyester chain obtained by the ring-opening polymerization. In this case, the hydroxy group contained in the reactive group R 2.
  • an alkyl chain, an ether chain, an ester chain, or an oligomer chain thereof is used as a substituent, and at least one reactive group is present in the substituent. It is particularly preferable that the substituent of the embodiment has been introduced into the cyclic molecule T.
  • the introduction rate of the substituent is as described in the introduction rate of the substituent.
  • the introduction rate of the reactive group R 1 into the cyclic molecule T is preferably 4 to 90%, particularly preferably 20 to 70%. If the introduction rate is less than 4%, the polyrotaxane (A) may not be sufficiently reacted with the (meth) acrylic acid ester copolymer (B) or the crosslinking agent (C). On the other hand, if the introduction rate exceeds 90%, a large number of crosslinks occur in the same cyclic molecule T, and thus the cyclic molecule T itself becomes a crosslink point, and the polyrotaxane (A) as a whole cannot exhibit the effect of the crosslink point. There is a possibility that sufficient stress relaxation property of the pressure-sensitive adhesive layer cannot be secured.
  • the blocking group BL of the polyrotaxane (A) is not particularly limited as long as the cyclic molecule T is a group that can maintain a skewered form with the linear molecule L.
  • Examples of such groups include bulky groups and ionic groups.
  • the block group BL of the polyrotaxane (A) may be a dinitrophenyl group, a cyclodextrin, an adamantane group, a trityl group, a fluorescein, a pyrene, an anthracene, or the like, or a number average molecular weight of 1,000.
  • a main chain or a side chain of a polymer of ⁇ 1,000,000 is preferable, and two or more of these blocking groups BL may be mixed in the polyrotaxane (A) or the pressure-sensitive adhesive composition.
  • Examples of the polymer having a number average molecular weight of 1,000 to 1,000,000 include polyamide, polyimide, polyurethane, polydimethylsiloxane, and polyacrylate.
  • the compounding amount of the polyrotaxane (A) in the pressure-sensitive adhesive composition is preferably formed by the pressure-sensitive adhesive composition, the reactive group R 3 equivalent ratio of the crosslinking agent (C) to the reactive group R 1 of the polyrotaxane (A).
  • the gel fraction and the haze value of the pressure-sensitive adhesive layer are appropriately adjusted so as to be within the above-mentioned range, but usually 0.05 to 30% by mass, preferably 0. 0% in the solid content of the pressure-sensitive adhesive composition.
  • the blending amount is 3 to 20% by mass.
  • the cyclic molecule T is preferably 0.1 to 60% when the maximum amount of the cyclic molecule T included in the skewered inclusion of the cyclic molecule T by the linear molecule L is 100%. More preferably, the linear molecules L are included in a skewered manner in an amount of 1 to 50%, particularly preferably 5 to 40%.
  • the maximum inclusion amount of the cyclic molecule T can be determined by the length of the linear molecule and the thickness of the cyclic molecule. For example, when the linear molecule is polyethylene glycol and the cyclic molecule is an ⁇ -cyclodextrin molecule, the maximum inclusion amount is experimentally determined (see Macromolecules 1993, 26, 5698-5703).
  • the (meth) acrylic acid ester which is a structural unit of the (meth) acrylic acid ester copolymer (B) is, for example, an alkyl group having 1 to 18 carbon atoms (meta ) (Meth) acrylate having an alicyclic compound such as an alkyl acrylate, cycloalkyl (meth) acrylate or the like as a functional group, (meth) acrylate having an aromatic compound such as benzyl (meth) acrylate as a functional group, etc. It is done.
  • (meth) acrylic acid alkyl esters having an alkyl group having 1 to 18 carbon atoms such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, and butyl (meth) acrylate. 2-ethylhexyl (meth) acrylate and the like. These may be used alone or in combination of two or more.
  • the reactive group-containing monomer which is a constituent unit of the (meth) acrylic acid ester copolymer (B), molecules a polymerizable double bond and a reactive group R 2 such as a hydroxy group, a carboxy group, and an amino group. It is a monomer contained in the inside. Two or more kinds of these reactive groups R 2 may be mixed in the (meth) acrylic acid ester copolymer (B).
  • the pressure-sensitive adhesive composition is not biased toward the acid side or the alkali side, is excellent in corrosion resistance, and is further stable in crosslinking of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition.
  • a hydroxy group is particularly preferable. Therefore, as the reactive group-containing monomer, a hydroxy group-containing unsaturated compound in which the reactive group R 2 is a hydroxy group is preferably used.
  • hydroxy group-containing unsaturated compound hydroxy group-containing unsaturated compound
  • hydroxy group-containing acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate are preferable, and these are used alone or in combination of two or more.
  • the (meth) acrylic acid ester copolymer (B) can be obtained by copolymerizing the above (meth) acrylic acid ester and a reactive group-containing monomer by a conventional method.
  • Vinyl formate, vinyl acetate, styrene and the like may be copolymerized in a small amount (for example, 10% by mass or less, preferably 5% by mass or less).
  • the mass average molecular weight of the (meth) acrylic acid ester copolymer (B) is preferably 100,000 to 3,000,000, particularly 500,000 to 2,000,000 in terms of GPC (Gel Permeation Chromatography). It is preferably 000,000. If the mass average molecular weight is less than 100,000, the pressure-sensitive adhesive layer may not have sufficient stress relaxation and durability. On the other hand, when the mass average molecular weight exceeds 3,000,000, the compatibility with the polyrotaxane (A) is deteriorated, the optical properties such as the total light transmittance of the pressure-sensitive adhesive layer are lowered, and the stress relaxation property is sufficient. May not be secured.
  • the glass transition temperature (Tg) of the (meth) acrylic acid ester copolymer (B) is preferably 50 ° C. or less, and particularly preferably 30 ° C. or less.
  • Tg glass transition temperature
  • the compatibility with the polyrotaxane (A) is deteriorated, and sufficient stress relaxation property of the pressure-sensitive adhesive layer may not be expressed.
  • the blending amount of the (meth) acrylic acid ester copolymer (B) in the pressure-sensitive adhesive composition is preferably the reactive group R 2 and the crosslinking agent (C) of the (meth) acrylic acid ester copolymer (B).
  • the equivalent ratio of the reactive group R 3 and the gel fraction of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition are appropriately adjusted so that they are within the above-described range.
  • the amount is 70 to 99.5% by mass, preferably 75 to 99% by mass in the minute.
  • the cross-linking agent (C) includes a reactive group R 3 possessed by the polyrotaxane (A) and a reactive group R 3 capable of reacting with the reactive group R 2 possessed by the (meth) acrylate copolymer (B).
  • the compound is not particularly limited as long as it has a bifunctional or higher compound.
  • the functional group R 3 possessed by the crosslinking agent (C) is preferably, for example, an isocyanate group, an epoxy group, an aziridine group, and particularly preferably an isocyanate group. Two or more of these functional groups R 3 may be present in the crosslinking agent (C).
  • the reactive group R 1 of the polyrotaxane (A) is a hydroxy group
  • the reactive group R 2 of the (meth) acrylate copolymer (B) is a hydroxy group
  • the reactive group R 3 of the crosslinking agent (C) is an isocyanate. If it is a group, the reaction proceeds at a controllable rate, so that the reactivity of the reactive group R 1 and the reactive group R 2 can be easily balanced.
  • the compound which has those reactive groups has high versatility, the kind of material is abundant, is easy to acquire, and can suppress cost low.
  • crosslinking agent (C) examples include isocyanate compounds such as xylylene diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, isophorone diisocyanate, and adducts thereof (for example, trimethylolpropane adduct), Epoxy compounds such as ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,6-hexanediol glycidyl ether, adducts thereof, N, N-hexamethylene-1,6-bis (1-aziridinecarboxyamide) And aziridine compounds such as adducts thereof, among which isocyanate compounds are preferred.
  • isocyanate compounds such as xylylene diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, isophorone diisocyanate, and adducts thereof (for example, trimethylolpropane
  • the compounding amount of the crosslinking agent (C) in the pressure-sensitive adhesive composition is preferably an equivalent ratio of the reactive group R 3 of the crosslinking agent (C) to the reactive group R 1 of the polyrotaxane (A), (meth) acrylic acid range ester copolymer (B) of the equivalent ratio of the reactive groups R 3 of the crosslinking agent (C) to reactive group R 2, and the gel fraction of the pressure-sensitive adhesive layer formed by the pressure-sensitive adhesive composition described above
  • the amount is adjusted as appropriate so that it is usually 0.1 to 10% by mass, preferably 0.5 to 5% by mass in the solid content of the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition may optionally contain a silane coupling agent (D) as a component other than the components (A) to (C).
  • a silane coupling agent (D) as a component other than the components (A) to (C).
  • adhesion between the obtained pressure-sensitive adhesive layer and an inorganic material such as a glass substrate can be improved.
  • the silane coupling agent (D) is not particularly limited, but has good compatibility with the components (A) to (C), and when the pressure-sensitive adhesive composition is used for optical purposes, What has a light transmittance is preferable.
  • silane coupling agent (D) examples include polymerizable unsaturated group-containing silicon compounds such as vinyltrimethoxysilane, vinyltriethoxysilane, and 3-methacryloyloxypropyltrimethoxysilane; 3-glycidyloxypropyltrimethoxysilane , Silicon compounds having an epoxy structure such as 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane; 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N Amino group-containing silicon compounds such as (2-aminoethyl) -3-aminopropylmethyldimethoxysilane; isocyanate group-containing silicon compounds such as 3-isocyanatopropyltriethoxysilane and 3-isocyanatopropyltrimethoxysilane; Trimethoxysilane
  • the addition amount of the silane coupling agent (D) is preferably in the range of 0.001 to 10 parts by mass, particularly 0.005 to 5 parts by mass with respect to 100 parts by mass of the total amount of the components (A) to (C).
  • the range of is preferable.
  • polyrotaxane (A) in which cyclic molecule T is ⁇ -cyclodextrin having a hydroxy group as reactive group R 1 , linear molecule L is polyethylene glycol, and block A polyrotaxane in which the group BL is an adamantane group is used, and a copolymer of butyl acrylate and hydroxyethyl acrylate (reactive group R 2 : hydroxy group) is used as the (meth) acrylic acid ester copolymer (B).
  • the trimethylolpropane adduct of xylylene diisocyanate (reactive group R 3 : isocyanate group) is used as the crosslinking agent (C).
  • the pressure-sensitive adhesive composition can be crosslinked by heating at a temperature of about 80 to 150 ° C. to form a pressure-sensitive adhesive layer.
  • the cyclic molecule T of the polyrotaxane (A) and the (meth) acrylic ester copolymer (B) are indirectly bonded via the crosslinking agent (C), and the cyclic molecule T is Since it moves freely on the linear molecule L of the polyrotaxane (A), the pressure-sensitive adhesive layer has excellent stress relaxation properties.
  • the pressure-sensitive adhesive layer has excellent optical characteristics such as total light transmittance and durability while maintaining stress relaxation properties.
  • the base material is not particularly limited, and any material used as a base material sheet for a normal pressure-sensitive adhesive sheet can be used.
  • woven fabric or non-woven fabric using fibers such as rayon, acrylic, polyester, etc .
  • paper such as fine paper, glassine paper, impregnated paper, coated paper
  • metal foil such as aluminum, copper; urethane foam, polyethylene foam, etc.
  • Polyester film such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyurethane film, polyethylene film, polypropylene film, polyvinyl chloride film, polyvinylidene chloride film, polyvinyl alcohol film, ethylene-vinyl acetate copolymer film , Polystyrene films, polycarbonate films, acrylic resin films, norbornene resin films, plastic films such as cycloolefin resin films; laminates of two or more of these It can gel.
  • the plastic film may be uniaxially stretched or biaxially stretched.
  • the substrate may be a release sheet or an optical member.
  • the release sheet include paper sheets such as glassine paper, clay coat paper, kraft paper, and high-quality paper, laminated paper obtained by laminating polyethylene paper to these papers, or a sheet base made of a plastic film such as polyethylene terephthalate or polyolefin.
  • Examples include a material in which a release agent such as a fluororesin or a silicone resin is applied and a release layer is provided by heat curing or ultraviolet curing.
  • examples of the optical member include a polarizing plate (polarizing film), a retardation plate (retarding film), a viewing angle compensation film, a brightness enhancement film, and a contrast enhancement film.
  • a polarizing plate (polarizing film) or a retardation plate (retardation film) is easily shrunk and has a large dimensional change compared to a general adherend, such as a substrate of a liquid crystal panel. It is suitable as an object to be formed.
  • the thickness of the optical member varies depending on the type, but is usually 10 ⁇ m to 500 ⁇ m, preferably 50 ⁇ m to 300 ⁇ m.
  • a pressure-sensitive adhesive layer is provided by directly applying a solution containing the pressure-sensitive adhesive composition (hereinafter sometimes referred to as “pressure-sensitive adhesive solution”) to the base sheet.
  • a pressure-sensitive adhesive solution may be applied on the release sheet to provide a pressure-sensitive adhesive layer, which is then attached to a base material sheet, and the pressure-sensitive adhesive layer may be transferred to the base material sheet.
  • examples of the solvent for diluting the pressure-sensitive adhesive composition to form a pressure-sensitive adhesive solution include aliphatic hydrocarbons such as hexane, heptane, and cyclohexane, aromatic hydrocarbons such as toluene and xylene, methylene chloride, and chloride.
  • Halogenated hydrocarbons such as ethylene, alcohols such as methanol, ethanol, propanol, butanol and 1-methoxy-2-propanol, ketones such as acetone, methyl ethyl ketone, 2-pentanone, isophorone and cyclohexanone, esters such as ethyl acetate and butyl acetate Cellosolve solvents such as ethyl cellosolve are used.
  • the concentration / viscosity of the pressure-sensitive adhesive solution prepared in this manner is not particularly limited as long as it can be coated, and can be appropriately selected according to the situation. Furthermore, if necessary, various additives such as an antioxidant, an ultraviolet absorber, a near infrared absorber, an antistatic agent, and a diffusing agent can be added to obtain a pressure-sensitive adhesive solution. In obtaining the pressure-sensitive adhesive solution, the addition of a solvent or the like is not a necessary condition, and the solvent may not be added as long as the viscosity can be coated by the pressure-sensitive adhesive composition. In this case, the pressure-sensitive adhesive composition is handled as it is as the pressure-sensitive adhesive solution.
  • the pressure-sensitive adhesive layer can be formed by removing the solvent by means such as hot air drying and reacting and crosslinking the pressure-sensitive adhesive composition by heating or the like.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited and is appropriately selected depending on the application, but is usually in the range of 5 to 100 ⁇ m, preferably 10 to 60 ⁇ m.
  • This pressure-sensitive adhesive sheet can absorb and relieve stress caused by the dimensional change with the pressure-sensitive adhesive layer even when the dimensional change of the substrate of the pressure-sensitive adhesive sheet or the adherend to which the pressure-sensitive adhesive sheet is attached is large. Therefore, it becomes difficult to peel off from the adherend over a long period of time.
  • a release sheet can be laminated on the surface of the pressure-sensitive adhesive layer on the side where the optical member is not laminated, if necessary.
  • the release sheet is peeled off, and when there is no release sheet, the glass substrate or the optical resin substrate is directly passed through the pressure-sensitive adhesive layer.
  • a liquid crystal panel, a liquid crystal display, a flexible display, an organic EL display, a display for electronic paper, and the like are configured.
  • the pressure-sensitive adhesive layer obtained by the pressure-sensitive adhesive composition has excellent optical properties such as total light transmittance and stress relaxation properties, and has a sufficient crosslinking density, so that it has excellent image display properties as a display and prevents light leakage. Excellent in durability and durability.
  • the sheet-like optical member for example, a sheet-like optical member such as a polarizing plate (polarizing film) or a retardation plate (retardation film) generally has a large dimensional change, but according to the pressure-sensitive adhesive sheet of the present invention having an optical member.
  • the stress that can be caused by the dimensional change of the sheet-like optical member can be absorbed and alleviated by the pressure-sensitive adhesive layer, and therefore it is difficult to peel off from the substrate or the like over a long period of time.
  • a modified polyrotaxane comprising a blocking group BL: adamantane group was prepared in the same manner as described in Soft Mater., 2008, 4, 245-249. The amount of hydroxy groups of the obtained polyrotaxane (A) was 1.4 mmol / g.
  • the polyrotaxane (A) (6 parts by mass) and the (meth) acrylic acid ester copolymer (B) have a weight average molecular weight of 180 consisting of 98.5% by mass of butyl acrylate units and 1.5% by mass of 2-hydroxyethyl acrylate units.
  • the pressure-sensitive adhesive composition obtained by mixing 4 parts by mass of 4 parts by mass and 0.2 part by mass of 3-glycidyloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM403) as the silane coupling agent (D) is obtained using methyl ethyl ketone. It diluted so that it might become a solution of solid content concentration 12%, and this was made into the adhesive solution.
  • the equivalent ratio of the isocyanate group of the crosslinking agent (C) to the hydroxy group of the polyrotaxane (A) is 1.5, and the hydroxy group of the (meth) acrylate copolymer (B)
  • the equivalent ratio of the isocyanate group of the crosslinking agent (C) to the group was 1.
  • the hydroxy group amount of the polyrotaxane (A) is a value measured based on JIS K0070.
  • the pressure-sensitive adhesive solution was coated on a release-treated surface of a polyethylene terephthalate release sheet (SP-PET3811, manufactured by Lintec Co., Ltd.), one side of which was removed with a silicone-based release agent, and dried at 90 ° C. for 1 minute.
  • a pressure-sensitive adhesive layer having a thickness of 25 ⁇ m was formed.
  • a polarizing plate triacetyl cellulose film / polyvinyl alcohol film / triacetyl cellulose film (including a viewing angle expansion function) three-layer laminate, thickness: 200 ⁇ m
  • a pressure-sensitive adhesive sheet on which a pressure-sensitive adhesive layer was formed was obtained.
  • Example 2 Except having adjusted the compounding quantity of a crosslinking agent (C) and a polyrotaxane (A) so that the equivalent ratio of the crosslinking agent (C) with respect to a (meth) acrylic acid ester copolymer (B) might be set to 0.5, Example In the same manner as in Example 1, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced.
  • Example 3 Except having adjusted the compounding quantity of a crosslinking agent (C) and a polyrotaxane (A) so that the equivalent ratio of the crosslinking agent (C) with respect to a (meth) acrylic acid ester copolymer (B) may be 0.2, Example In the same manner as in Example 1, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced.
  • Example 4 Except having adjusted the compounding quantity of a crosslinking agent (C) and a polyrotaxane (A) so that the equivalent ratio of the crosslinking agent (C) with respect to a (meth) acrylic acid ester copolymer (B) may be set to 0.1, it is an Example.
  • a polarizing plate with an adhesive was prepared.
  • Example 5 Except having adjusted the compounding quantity of a crosslinking agent (C) and a polyrotaxane (A) so that the equivalent ratio of the crosslinking agent (C) with respect to a (meth) acrylic acid ester copolymer (B) might be set to 0.01, Example In the same manner as in Example 1, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced.
  • Example 6 Example 1 except that the blending amount of the crosslinking agent (C) and the (meth) acrylate copolymer (B) was adjusted so that the equivalent ratio of the crosslinking agent (C) to the polyrotaxane (A) was 2. Similarly, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced.
  • Example 7 Example 1 except that the blending amount of the crosslinking agent (C) and the (meth) acrylic acid ester copolymer (B) was adjusted so that the equivalent ratio of the crosslinking agent (C) to the polyrotaxane (A) was 4. Similarly, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced.
  • a pressure-sensitive adhesive composition mixed with 0.2 part by mass of methoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM403) was diluted with methyl ethyl ketone so as to be a solution having a solid content concentration of 12%, and this was used as a pressure-sensitive adhesive solution.
  • the equivalent ratio of the isocyanate group of the crosslinking agent (C) with respect to the hydroxy group of the (meth) acrylic acid ester copolymer (B) was 1.
  • a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced in the same manner as in Example 1 except that the obtained pressure-sensitive adhesive solution was used.
  • Acrylic acid having a mass average molecular weight of 800,000 comprising 5 parts by mass of the polyrotaxane (A) and 80% by mass of butyl acrylate units and 20% by mass of 2-hydroxyethyl acrylate units as the (meth) acrylic acid ester copolymer (B).
  • a pressure-sensitive adhesive composition obtained by mixing 100 parts by mass of an ester copolymer and 2.5 parts by mass of a xylylene diisocyanate trimethylolpropane adduct (TD-75, manufactured by Soken Chemical Co., Ltd.) as a crosslinking agent (C). The solution was diluted with methyl ethyl ketone so that the solution had a solid concentration of 12%, and this was used as an adhesive solution.
  • the equivalent ratio of the isocyanate group of the crosslinking agent (C) with respect to a polyrotaxane (A) is 0.8, and the crosslinking agent with respect to the hydroxyl group of the (meth) acrylic acid ester copolymer (B) ( The equivalent ratio of isocyanate groups in C) was 0.05.
  • Adhesive prepared by mixing 100 parts by mass of 800,000 acrylate copolymer and 10 parts by mass of xylylene diisocyanate trimethylolpropane adduct (TD-75, manufactured by Soken Chemical Co., Ltd.) as a crosslinking agent (C)
  • the composition was diluted with methyl ethyl ketone so as to be a solution having a solid concentration of 12%, and this was used as an adhesive solution.
  • the equivalent ratio of the isocyanate group of the crosslinking agent (C) with respect to a polyrotaxane (A) is 0.8, and the crosslinking agent with respect to the hydroxyl group of the (meth) acrylic acid ester copolymer (B) ( The equivalent ratio of isocyanate groups in C) was 0.2.
  • a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a polarizing plate was produced in the same manner as in Example 1 except that the obtained pressure-sensitive adhesive solution was used.
  • the amount of deviation ( ⁇ m) of the pressure-sensitive adhesive sheet after 70,000 seconds was measured according to the measuring method for holding power of JIS Z0237 except that the measurement temperature was 80 ° C. The results are shown in Table 1.
  • a plurality of the pressure-sensitive adhesive layers are laminated so that the total thickness of the pressure-sensitive adhesive layers in the pressure-sensitive adhesive sheet is 1 mm and only the release sheet of the double-sided outermost layer remains, and the atmosphere is 23 ° C. and a humidity of 50%. Left for 2 weeks. Thereafter, a 10 mm wide ⁇ 100 mm long sample is cut out from the pressure-sensitive adhesive sheet in which a plurality of the pressure-sensitive adhesive layers are laminated, and the release sheet laminated on the double-sided outermost layer is peeled off so that the sample measurement range is 10 mm wide ⁇ 500 mm long.
  • the elongation at break (%) was measured at a tensile rate of 10 mm / min using a tensile tester (Orientec, Tensilon) in an environment of 23 ° C. and 50% RH. The results are shown in Table 1.
  • the pressure-sensitive adhesive solutions used in the examples and comparative examples were dried on the release-treated surface of a polyethylene terephthalate release sheet (SP-PET3811, manufactured by Lintec Co., Ltd.) on which one side was release-treated with a silicone-based release agent. It apply
  • the pressure-sensitive adhesive layer was bonded to the release-treated surface of another polyethylene terephthalate release sheet (manufactured by Lintec Corporation, SP-PET3801) to obtain a pressure-sensitive adhesive sheet.
  • the adhesive sheet is allowed to stand for 1 week in an atmosphere of 23 ° C. and 50% humidity. Then, about 0.1 g of the adhesive is taken out from the adhesive sheet, wrapped in Tetron mesh (# 400), and Soxhlet using ethyl acetate as a solvent.
  • the non-gel content of the pressure-sensitive adhesive was extracted by refluxing using an extraction apparatus (manufactured by Tokyo Glass Instrument Co., Ltd., fat extractor), and the gel fraction was calculated from the ratio to the initial mass. The results are shown in Table 1.
  • the pressure-sensitive adhesive sheet in which the pressure-sensitive adhesive layer was formed on the polarizing plates obtained in Examples and Comparative Examples was 233 mm ⁇ 309 mm in size using a cutting device (Super Cutter PN1-600, manufactured by Sugano Seiki Seisakusho Co., Ltd.) And then bonded to one side of an alkali-free glass (Corning Corp., 1737, thickness: 0.7 mm) and placed in an autoclave (Kurihara Seisakusho Co., Ltd.) at 0.5 MPa, 50 ° C. for 20 minutes.
  • the optical laminate was obtained by pressurizing under the conditions described above.
  • the obtained optical laminate was put in an environment under the following durability conditions.
  • ⁇ Durability conditions > 1.60 ° C, relative humidity 90% 2. 80 ° C./dry 3. 200 cycles of heat shock test at -20 °C ⁇ ⁇ 60 °C for 30 minutes each
  • the pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layer formed on the polarizing plates obtained in Examples and Comparative Examples was 233 mm ⁇ 309 mm by a cutting device (Super Cutter PN1-600, manufactured by Sugano Seiki Seisakusho Co., Ltd.). Cut to size, bonded to both surfaces of alkali-free glass (Corning, 1737, thickness: 0.7 mm), and 0.5 MPa, 50 ° C., 20 in an autoclave (Kurihara Seisakusho). Pressurization was performed under the condition of minutes to obtain an optical laminate. In addition, the said bonding was performed so that the polarization axis of the polarizing plate of both surfaces of this optical laminated body might be in a crossed Nicol state in the front and back of an alkali free glass.
  • the obtained optical layered body was allowed to stand at 80 ° C. for 200 hours, then left in an environment at 23 ° C. and 50% relative humidity for 2 hours, and light leakage was evaluated by the following method.
  • the pressure-sensitive adhesive layer and the pressure-sensitive adhesive sheet of the example were excellent in all of durability, light leakage, and optical characteristics.
  • Comparative Example 1 corresponds to a so-called conventional hard pressure-sensitive adhesive layer having a small elongation at break although the holding force is within the range of the present invention.
  • Comparative Example 1 although the same (meth) acrylic acid ester copolymer (B) as in the example was used, durability and light leakage prevention were insufficient.
  • Comparative Example 2 corresponds to a so-called conventional soft pressure-sensitive adhesive layer rich in stress relaxation property that falls in the measurement of holding power, although the elongation at break is within the range of the present invention. Even in Comparative Example 2 as described above, durability and light leakage prevention were insufficient as compared with Examples using the same (meth) acrylic acid ester copolymer (B).
  • Comparative Example 3 corresponds to Example 6 in which the amount of deviation in the measurement of the holding force at normal temperature was the smallest among the examples disclosed in Japanese Patent Application Laid-Open No. 2007-224133.
  • the elongation at break was outside the range of the present invention, and both durability and light leakage prevention were insufficient.
  • Comparative Example 4 is an example in which the polyrotaxane content is increased in the same system as Comparative Example 3 from the viewpoint of increasing the holding power, and corresponds to Example 7 of the above document.
  • both the breaking elongation and the holding force (deviation amount) are within the scope of the present invention, but the haze value is outside the scope of the present invention. From the results of Comparative Example 4, it can be seen that durability and light leakage prevention are insufficient even when the haze value does not satisfy the present invention.
  • prescribed (meth) acrylic acid ester copolymer (B) is used, In that respect, it differs from the Example of the said literature.
  • the pressure-sensitive adhesive sheet of the present invention is suitable as an adhesive polarizing plate or a retardation plate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Ceramic Engineering (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)
  • Polarising Elements (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

La feuille adhésive est telle qu’elle comprend d’une part un matériau de base, d’autre part une couche d’adhésif formée d’une composition adhésive, dans laquelle une molécule à chaîne linéaire perce au moins deux cavités d’une molécule cyclique, qui possède, dans la molécule cyclique susmentionnée, au moins un groupe réactif, et qui possède (A) un polyrotaxane possédant un groupe bloc aux deux extrémités de la molécule à chaîne linéaire susmentionnée. Le degré d’allongement à la rupture de la couche d’adhésif susmentionnée est supérieur ou égal à 300% et la valeur de voile est inférieure ou égale à 30%. Et, sauf lorsque la température mesurée est de 80°C, la force de retenue de la feuille adhésive susmentionnée conformément à JIS Z0237, en tant que décalage de la feuille adhésive susmentionnée 70000 secondes plus tard, est inférieure ou égale à 1000μm. Cette feuille adhésive et sa couche d’adhésif, lorsqu’elles sont utilisées comme élément optique par exemple dans une plaque de polarisation ou une plaque de déphasage, garantissent de façon satisfaisante des propriétés optiques telles que le facteur de transmission totale de la lumière et présentent d’excellentes propriétés de relaxation en contrainte, de prévention de fuites de lumière et de durée de vie.
PCT/JP2009/070315 2008-12-10 2009-12-03 Feuille adhésive Ceased WO2010067745A1 (fr)

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US13/133,731 US20110262746A1 (en) 2008-12-10 2009-12-03 Pressure-sensitive adhesive sheet
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WO2018021267A1 (fr) * 2016-07-25 2018-02-01 国立大学法人 東京大学 Pseudopolyrotaxane, polyrotaxane, et procédés de production de pseudopolyrotaxane et de polyrotaxane
JP2018045213A (ja) * 2016-09-16 2018-03-22 リンテック株式会社 フレキシブルディスプレイ用粘着剤、粘着シート、フレキシブル積層部材およびフレキシブルディスプレイ
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CN103360997A (zh) * 2012-03-30 2013-10-23 琳得科株式会社 粘着性组合物，粘着剂以及粘着片
CN103360997B (zh) * 2012-03-30 2016-08-17 琳得科株式会社 粘着性组合物，粘着剂以及粘着片
WO2018021267A1 (fr) * 2016-07-25 2018-02-01 国立大学法人 東京大学 Pseudopolyrotaxane, polyrotaxane, et procédés de production de pseudopolyrotaxane et de polyrotaxane
JP2018045213A (ja) * 2016-09-16 2018-03-22 リンテック株式会社 フレキシブルディスプレイ用粘着剤、粘着シート、フレキシブル積層部材およびフレキシブルディスプレイ
JP2020109177A (ja) * 2020-02-28 2020-07-16 リンテック株式会社 フレキシブルディスプレイ用粘着シート、フレキシブル積層部材およびフレキシブルディスプレイ
JP7069234B2 (ja) 2020-02-28 2022-05-17 リンテック株式会社 フレキシブルディスプレイ用粘着シート、フレキシブル積層部材およびフレキシブルディスプレイ

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JP2010138259A (ja) 2010-06-24

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